Methanol → HCID 10172313, compound

Participants

Reaction Steps

To a solution of 6-(4-chlorophenyl)-5-(phenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid (50 mg, 0.15 mmol) from Example 1, Step C (containing a trace of the 3-nitrile starting material) in methylene chloride (3 mL) and methanol (1 mL) was added 2M trimethylsilyldiazomethane in hexanes until the yellow color persisted. The volatiles were removed under a stream of nitrogen and the residue was separated by preparative TLC on silica gel (eluted with 30% ethyl acetate in hexanes) to obtain 2-(methoxy)-6-(4-chlorophenyl)-5-(phenyl)pyridine-3-nitrile (A) and methyl 2-(methoxy)-6-(4-chlorophenyl)-5-(phenyl)pyridine-3-carboxylate (B) as minor products (along with some of the N-alkylation by-products). The main product was the expected methyl 6-(4-chlorophenyl)-5-(phenyl)-2-oxo-1,2-dihydropyridine-3-carboxylate (same product as obtained in Example 1, Step D).

Provenance & Evidence